Ashland Vacation Rentals

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Dec 28 - Dec 29
Tomorrow
Dec 29 - Dec 30
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Ashland vacation rentals

Exterior
Charming 3-bedroom house in delightful Ashland for your getaway

Charming 3-bedroom house in delightful Ashland for your getaway

Charming 3-bedroom house in delightful Ashland for your getaway
2.0 star property
Ashland
$262 nightly
The price is $277
Jan 2 - Jan 3, 2026
Total with taxes and fees
Charming 3-bedroom house in delightful Ashland for your getaway
Exterior
Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St
2.0 star property
Back Bay
8.2 out of 10, Very Good, (155)
"Room was clean and a good size. Location was perfect - walking distance to where I needed to be. "
United States
Steven
$194 nightly
The price is $223
Jan 4 - Jan 5, 2026
Total with taxes and fees
Maverick Suites at 245 Newbury St
42-inch TV with satellite channels
Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.2 out of 10, Good, (134)
"Good location, compact room with everything you need. Very convenient self-service token-operated washing machine and dryer. Worth the price. No elevators, and bed is a bit small."
United Kingdom
Fanny Pei Yee
$185 nightly
The price is $213
Dec 29 - Dec 30
Total with taxes and fees
Maverick Suites at 400 Columbus Ave
Deluxe Studio Suite (2nd Floor - Unit 202) | Individually furnished, iron/ironing board, free WiFi, bed sheets
Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway

Maverick Suites at 28 Fenway
3.0 star property
Fenway–Kenmore
8.6 out of 10, Excellent, (330)
"Good place"
United States
Elijah
$190 nightly
The price is $218
Jan 5 - Jan 6, 2026
Total with taxes and fees
Maverick Suites at 28 Fenway
Iron/ironing board, WiFi, bed sheets
The Chester: Hip, Renovated, South End

The Chester: Hip, Renovated, South End

The Chester: Hip, Renovated, South End
2.0 star property
South End
10.0 out of 10, Exceptional, (2)
"Nice room. Good location "
United States
Abenamar A.
$299 nightly
The price is $343
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Chester: Hip, Renovated, South End
City Studio | Egyptian cotton sheets, premium bedding, memory foam beds
The Chester Hotel

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (28)
"Had a great stay. Super convenient to Northeastern and shopping/restaurants. "
United States
kelly
$319 nightly
The price is $367
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Chester Hotel
Exterior
Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential

Stylish Back Bay Retreat, Steps from Prudential
Back Bay
8.6 out of 10, Excellent, (7)
"Beautiful place right on historic Newbury Street. I’ll definitely return and I’d highly recommend this apartment."
United States
JEANPAUL
$276 nightly
The price is $297
Dec 29 - Dec 30
Total with taxes and fees
Stylish Back Bay Retreat, Steps from Prudential
Apartment | Premium bedding, desk, iron/ironing board, free WiFi
Charlesgate Suites

Charlesgate Suites

Charlesgate Suites
3.5 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (201)
"New spot for us in South Bay. Convenient and easy with easy walk to Commonwealth and restaurants of Newbury"
United States
Brian
$302 nightly
The price is $347
Jan 2 - Jan 3, 2026
Total with taxes and fees
Charlesgate Suites
Fridge, microwave, oven, stovetop
Charming single family Cottage, pet friendly w fenced in yard,

Charming single family Cottage, pet friendly w fenced in yard,

Charming single family Cottage, pet friendly w fenced in yard,
2.0 star property
Lincoln
10.0 out of 10, Exceptional, (20)
"Booked this cozy cottage for a night as we attended a concert at Gillette Stadium. An easy 20 minute drive to and from the stadium. "
United States
Sarah K.
$180 nightly
The price is $194
Dec 30 - Dec 31
Total with taxes and fees
Charming single family Cottage, pet friendly w fenced in yard,
Interior
Hidden Gem right in the city of Boston!

Hidden Gem right in the city of Boston!

Hidden Gem right in the city of Boston!
Hyde Park
9.6 out of 10, Exceptional, (25)
"We were in town for a conference for work and didn't want to stay in a hotel. The place was very clean and smelled amazing. Perfect space 3 friends to stay. Host was great she answered when reaching out before the stay and the arrival was seamless."
United States
TIARA V.
$285 nightly
The price is $327
Jan 6 - Jan 7, 2026
Total with taxes and fees
Hidden Gem right in the city of Boston!
Exterior
✨Private Studio w/ Loft Center Historic Carlisle✨

✨Private Studio w/ Loft Center Historic Carlisle✨

✨Private Studio w/ Loft Center Historic Carlisle✨
Carlisle
9.4 out of 10, Exceptional, (33)
"We had a great stay! The place was perfect for our weekend trip. We were able to hit all of the spots we planned, with the central location!"
United States
C Z.
$149 nightly
The price is $157
Dec 30 - Dec 31
Total with taxes and fees
✨Private Studio w/ Loft Center Historic Carlisle✨
Exterior
The Chester: Modern Luxury, Historic Charm

The Chester: Modern Luxury, Historic Charm

The Chester: Modern Luxury, Historic Charm
2.0 star property
South End
9.0 out of 10, Wonderful, (2)
"Easy check in. Clean space. Cute decor and comfortable. Husband and I enjoyed the location. "
United States
Morgan Z.
$299 nightly
The price is $343
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Chester: Modern Luxury, Historic Charm
Desk, iron/ironing board, WiFi, bed sheets
The Chester: Urban Chic Retreat In South End

The Chester: Urban Chic Retreat In South End

The Chester: Urban Chic Retreat In South End
2.0 star property
South End
10.0 out of 10, Exceptional, (1)
"We had a great stay in Boston and the Chester was perfect for our trip. First time in Boston so we did a lot of the usual things, but this location was great to easily connect with bus and train options as we decided not to rent a vehicle. Space was comfortable for group of three - lots of shops and restaurants in the area. We were touring a lot, so didn’t spend a lot of time in the unit, but it was very comfortable and would definitely come back again!"
United States
Chad T.
$331 nightly
The price is $380
Dec 29 - Dec 30
Total with taxes and fees
The Chester: Urban Chic Retreat In South End
Interior entrance
Maverick Suites at 89 Marion

Maverick Suites at 89 Marion

Maverick Suites at 89 Marion
2.0 star property
Coolidge Corner South Side
8.2 out of 10, Very Good, (270)
"Had an amazing time. Loved the property and it's location in proximity to entertainment, transportation, dining and scenic entertainment. "
United States
Nicole
$182 nightly
The price is $203
Jan 4 - Jan 5, 2026
Total with taxes and fees
Maverick Suites at 89 Marion
Exterior
Cozy Adventure filled Escape

Cozy Adventure filled Escape

Cozy Adventure filled Escape
2.0 star property
Worcester
10.0 out of 10, Exceptional, (1)
"The rooms were cozy and clean. The radiant heat felt great. The building was solid and sounds from other guests were muted. The host was also friendly. "
United States
Craig
$239 nightly
The price is $274
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy Adventure filled Escape
Property grounds
Crescent Suites Hotel

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1145)
"Lovely, quiet place."
United States
Fatu
$140 nightly
The price is $157
Jan 1 - Jan 2, 2026
Total with taxes and fees
Crescent Suites Hotel
Interior
558/1 - 3BR Boston - Modern Nest near Franklin Park

558/1 - 3BR Boston - Modern Nest near Franklin Park

558/1 - 3BR Boston - Modern Nest near Franklin Park
Dorchester
9.2 out of 10, Wonderful, (9)
"Overall our stay was great. The unit we stayed in was clean and comfortable. The host was very kind, helpful, and accommodating. "
United States
Jessica M.
$306 nightly
The price is $352
Dec 29 - Dec 30
Total with taxes and fees
558/1 - 3BR Boston - Modern Nest near Franklin Park
Apartment, 2 Bedrooms | Private kitchen | Mini-fridge, microwave, cookware/dishes/utensils, paper towels
Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
7.8 out of 10, Good, (68)
"Loved how cozy and clean it was. Location was great, near many points of interest. Parking at an extra fee, but plenty of street parking in the area. "
United States
Isaiah Joel Santa
$185 nightly
The price is $213
Dec 29 - Dec 30
Total with taxes and fees
Maverick Suites at 402 Columbus Ave
WiFi, bed sheets
The Chester: Vintage Elegance, Modern Comfort

The Chester: Vintage Elegance, Modern Comfort

The Chester: Vintage Elegance, Modern Comfort
2.0 star property
South End
$299 nightly
The price is $343
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Chester: Vintage Elegance, Modern Comfort
TV
Charming 2-bedroom apartment in Cambridge with AC near Harvard Tufts porter sq

Charming 2-bedroom apartment in Cambridge with AC near Harvard Tufts porter sq

Charming 2-bedroom apartment in Cambridge with AC near Harvard Tufts porter sq
North Cambridge
$214 nightly
The price is $245
Jan 10 - Jan 11, 2026
Total with taxes and fees
Charming 2-bedroom apartment in Cambridge with AC near Harvard Tufts porter sq
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ashland Hotel Reviews

Midtown Hotel

Midtown Hotel

10/10 Excellent
"Room is amazing. Very clean and comfortable. Quiet and nice. "
Yunny 1-night trip
Posted 17 hours ago
Midtown Hotel

Find out more about Ashland

Everything you need to know about Ashland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ashland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Ashland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $130 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Ashland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Ashland?

Yes, you can find vacation rentals near top local attractions in Ashland, or you can go with a more secluded option if you're looking for relaxation. Ashland is known for its shopping and restaurants. Make sure you have time to check out the lake views while you're in the area.

What are some of the best vacation rentals that Ashland has to offer?

Hidden Gem right in the city of Boston!: Visitors like this Ashland vacation home rental. It is located near skiing and offers a selection of games, air-conditioning, and a Smart TV to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Ashland?

While exploring the area, visit family-friendly sights like Fun and Games Family Entertainment Center, or get outside and enjoy nature at Cochituate State Park. Other places in town to visit include Hopkinton State Park and Ashland State Park.

What are vacation rentals like in Ashland?

Vacation rentals are private properties you can reserve for a couple days or more in Ashland. Vacation rentals provide amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.